Chlorbufam
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Chlorbufam
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CAS No:
1967-16-4
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Formula:
C11H10ClNO2
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Chemical Name:
Chlorbufam
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Synonyms:
Carbamic acid,N-(3-chlorophenyl)-,1-methyl-2-propyn-1-yl ester;Carbanilic acid,m-chloro-,1-methyl-2-propynyl ester;Carbamic acid,(3-chlorophenyl)-,1-methyl-2-propynyl ester;1-Butyn-3-yl m-chlorophenylcarbamate;3-Chlorophenylcarbamic acid 1-methylpropynyl ester;BIPC;Chlorbufam;Chlorobufam;Grisemin;3-Butyn-2-yl m-chlorocarbanilate;Chlorbupham;1-Methyl-2-propynyl N-(3-chlorophenyl)carbamate
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CAS No:
Characteristics
38.3
3.59
1.22 g/cm3
45-46 °C
270.0±25.0 °C(Predicted)
117.1ºC
1.5500 (estimate)
In water, 540 mg/L at 20 deg C
0-6°C
2.1 m Pa /1.58X10-5 mm Hg/ at 20 deg C
Oral-Rat LD50: 2380 mg/kg; Abdominal cavity-mouse LD50: 250 mg/kg
Combustion produces toxic nitrogen oxides and chloride gases
Henry's Law constant: 8.6X10-9 atm-cu m/mol at 20 °C /Estimated/
Changes color when exposed to light. Unstable in strong acidic and alkaline solutions. Stable up to 40 °C. Alcohols may cause trans esterification.|Hydroxyl radical reaction rate constant = 4.6X10-11 cu m/molecule-sec at 25 °C /Estimated/|Ozone rate constant = 3X10-20 cu cm/molec-sec at 25 °C /Estimated/
Safety Information
UN30779/PG3
51/53
61
FD8575000
N
Warehouse ventilated, low temperature and dry
Unstable in strongly acidic and alkaline media (l>pH>13). Changes color when exposed to light. Alcohols may cause trans-esterification. Stable up to 40 deg C.
P273-P391-P501
H411
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
|H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]|P273, P391, and P501|Aggregated GHS information provided by 41 companies from 2 notifications to the ECHA C&L Inventory.
Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, not otherwise specified (compounds and preparations) (agricultural insecticides, nec, liquid)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear positive pressure self-contained breathing apparatus. ... Wear appropriate chemical protective clothing. /Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Wear appropriate chemical protective gloves, boots and goggles. ... Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec); Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/
Extinguish fire using agent suitable for type of surrounding fire. Material itself does not burn or burns with difficulty. /Carbaryl (agricultural insecticides, nec, liquid); Carbaryl (agricultural insecticides, nec, other than liquid); Carbaryl (insecticides, other than agricultural, nec/|If material /is/ on fire or involved in /a/ fire do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, liquid, nos, (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (agricultural insecticides, nec, liquid); Carbamate pesticide, liquid, nos (compounds and preparations) (insecticides, other than agricultural, nec/|Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, liquid nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use "alcohol" foam, dry chemical or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (insecticides, other than agricultural, nec)/|Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. /Carbamate pesticide, solid, nos (compounds and preparations) (agricultural insecticides, nec, other than liquid)/
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
Carbamates produce slight to moderate skin and eye irritation, depending on the vehicle used, duration of contact, and on whether the substance is applied to the abraided or intact skin. From the available data, it cannot be excluded that some of the carbamates will have a slight to moderate sensitization potential. /Carbamate Pesticides/
Toxicity
moderately toxic
A greater than additive effect on lethal dose (LD50 469.5 mg/kg body wt) was found for the combined administration of chlorbufam and parathion to NMRI mice.
LD50 Mouse ip 250 mg/kg|LD50 Rat oral 2380 mg/kg
/BIRDS and MAMMALS/ As a rule, birds are not very sensitive to carbamates. /Carbamate pesticides/|/OTHER TERRESTRIAL SPECIES/ Bees are extremely sensitive. /Carbamate pesticides/
Chlorbufam's former production and use as a herbicide(1) resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: IT PERSISTS IN SANDY LOAM FOR ABOUT 56 DAYS.|TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 162(2), indicates that chlorbufam is expected to have very moderate mobility in soil(SRC). Volatilization of chlorbufam from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 8.6X10-9 atm-cu m/mole(SRC), based upon its vapor pressure, 1.58X10-5 mm Hg(3), and water solubility, 540 mg/L(3). Chlorbufam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(3). An 85% biodegradation loss in 10 days when incubated in soil(4) indicates that biodegradation may be an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), a Koc value of 162(2), indicates that chlorbufam may adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 8.6X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.58X10-5 mm Hg(4), and water solubility, 540 mg/L(4). According to a classification scheme(5), an estimated BCF of 120(SRC), from its log Kow of 3.59(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is high(SRC). Hydrolysis of chlorbufam probably occurs in two steps, from the oxazolidine to the 3-chloroaniline(8,9). An 85% biodegradation loss in 10 days when incubated in soil(8) indicates that biodegradation may be an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), chlorbufam, which has a vapor pressure of 1.58X10-5 mm Hg at 20 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase chlorbufam is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 8.3 hours(SRC), calculated from its rate constant of 4.6X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase chlorbufam may be removed from the air by wet and dry deposition(SRC).
The rate constant for the vapor-phase reaction of chlorbufam with photochemically-produced hydroxyl radicals has been estimated as 4.6X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8.3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of chlorbufam with ozone has been estimated as 3X10-20 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 382 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Hydrolysis of chlorbufam probably occurs in two steps, from the oxazolidine to the 3-chloroaniline(3,4). Hydrolysis is rapid in basic media (k = 1.97X10+4 /sec at 30 °C, pH = 11)(3).
An estimated BCF of 116 was calculated for chlorbufam(SRC), using a log Kow of 3.59(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is high(SRC), provided the compound is not altered physically or chemically once released into the environment(SRP).
162.18 L/kg|The Koc for chlorbufam has been reported to be 162(1). According to a classification scheme(2), this Koc value suggests that chlorbufam is expected to have moderate mobility in soil. The 3-chloroaniline metabolite will be covalently bound to humic material. An increase in soil organic matter resulted in an increase in the adsorption of chlorbufam(3).
The estimated Henry's Law constant for chlorbufam is 8.6X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 1.58X10-5 mm Hg(1), and water solubility, 540 mg/L(1). This Henry's Law constant indicates that chlorbufam is expected to be essentially nonvolatile from moist soil(SRC) and water surfaces(2). Chlorbufam is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
Occupational exposure and general population exposure should be low or non-existent since chlorbufam is no longer produced or used. In the past, chlorbufam was applied directly to the grass, onion and other crops as an herbicide and exposure to this compound was primarily by inhalation of particles and dermal contact. (SRC)
Drug Information
3. 3= Moderately toxic: Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz and 1 pint (or 1 lb) for 70 kg person (150 lb). /Chlorpropham/
Chlorpropham and propham (and presumably chlorbufam) are metabolized by para-ring hydroxylation, carbamate hydrolysis, and side-chain oxidation. /Chlorpropham/|The first step in the metabolism of carbamates is hydrolysis to carbamic acid, which decomposes to carbon dioxide (CO2) and the corresponding amine. The mechanism of hydrolysis is different for N -methyl and N -dimethyl derivatives. The N -methyl carbamates pass through an isocyanate intermediate, whereas in the hydrolysis of N - dimethylcarbamates, an addition product with a hydroxyl ion is formed yielding the alcohol and N -dimethyl substituted acid. The rate of hydrolysis by esterases is faster in mammals than in plants and insects. Apart from hydrolysis, oxidation also takes place including: hydroxylation of the aromatic ring, O -dealkylation, N -methyl hydroxylation, N -dealkylation, oxidation of aliphatic side chains, and sulfoxidation to the corresponding sulfone. Oxidation is associated with the mixed-function oxidase (MFO) enzymes. Conjugation leads to the formation of O - and N -glucuronides, sulfates, and mercapturic acid derivatives in mammals. Glycosides and phosphates are conjugation products more common in plants. /Carbamate Pesticides/
Skin contamination should be treated promptly by washing with soap and water. Contamination of the eyes should be treated immediately by prolonged flushing of the eyes with large amounts of clean water. If dermal or ocular irritation persists, medical attention should be obtained without delay. /Other Herbicides/|If serious dehydration and electrolyte depletion have occurred as a result of vomiting and diarrhea, monitor blood electrolytes and and fluid balance and administer intravenous infusions of glucose, normal saline ringer's solution, or ringer's lactate to restore extracellular fluid volume and electrolytes. Follow this with oral nutrients as soon as fluids can be retained. Fluids serve to support excretion of the toxicants. Supportive measures are ordinarily sufficient for successful management of excessive exposures to these herbicides. /Other Herbicides/
1-butyn-3-yl 3-chlorophenylcarbamate
Chlorbufam Use and Manufacturing
Produced by reaction of 3-chlorophenyl isocyanate and 1-methylprop-2-yn-l-ol...|m-Chloroaniline + phosgene + 3-butyn-2-ol(phosgenation/isocyanate addition)
For chlorbufam (USEPA/OPP Pesticide Code: 575200) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./|Selective herbicide. Inhibits photosynthesis. Normally used in combination with other herbicides for pre-emergence control of grasses and broad-leaved weeds in onions, leeks, garlic, shallots, carrots, beet, spinach, sunflowers, and bulb flowers.
...Generally used as a mixture with chloridazon ... `Alicep'...a mixt with chloridazon, `Alipur'...a mixt with cycluron is no longer available.
The WHO Recommended Classification of Pesticides by Hazard identifies Chlorbufam (technical grade) as an active ingredient believed to be obsolete or discontinued for use as a pesticide.|Introduced by BASF AG (Federal Republic of Germany Patent 1,034,912; 1,062,482)... Chlorbufam is...generally used as a mixture with chloridazon at 3-6 kg product/ha (for use in flower-bulb crops, leeks and onions). The main Weeds controlled are: Apera spica-venti, Raphanus raphanistrum, Sinapsis alba, Stellaria media, Urtica circus, Atriplex, Matricaria, Poa and Polygonum species.|Alicep*: discontinued by BASF AG.|Compatible with some other herbicides, but incompatible with alkaline materials.
PRODUCT ANALYSIS IS BY ACID HYDROLYSIS TO 3-CHLOROANILINE, DETERMINED BY TITRATION. RESIDUES MAY BE DETERMINED BY HYDROLYSIS AND COLORIMETRY OF THE RESULTING 3-CHLOROANILINE, OR BY GC.|DESCRIPTION IS GIVEN FOR GAS CHROMATOGRAPHIC QUANT ANALYSIS OF A MODEL WATER SAMPLE CONTAINING 8 CARBAMATES WHICH ARE INCREASINGLY USED AS HERBICIDES & INSECTICIDES. THE METHOD IS APPLICABLE TO A CONCN OF BETWEEN 5-50 NG CARBAMATE/L OF DRINKING OR NON-POLLUTED GROUND WATER. RECOVERY RATE IN COMMUNAL WASTE WATER WAS 92% CHLORBUFAM.
Agrochemicals -> Herbicides
Computed Properties
Molecular Weight:223.65
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:223.0400063
Monoisotopic Mass:223.0400063
Topological Polar Surface Area:38.3
Heavy Atom Count:15
Complexity:271
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes